1-palmitoyl-2-linoleoyl-3-acetylglycerol (PLA), one of the compounds of Formula 1, is separated from the chloroform extracts of a deer antler, and is known as having activities for proliferation of hematopoietic stem cells and megakaryocytes (Korean Patent No. 10-0283010). As the processes for preparing the compound of Formula 1, a method of synthesizing the compound from glycerol and a method of acetolysis of phosphatidyl choline are known (Korean Patent Application No. 10-2000-0045168). However, the method of synthesizing the compound of Formula 1 from glycerol is not a regioselective process, and thus requires separation and purification steps using a column-chromatography after each reaction step. Namely, the target compound (PLA) can be obtained by the steps of separating 1-palmitoylglycerol by using a column chromatography from the reaction product of glycerol and palmitic acid, and successively esterifying the separated 1-palmitoylglycerol. The method has drawbacks that the yield is very low(about 3.21% from glycerol), and one equivalent of expensive 4-dimethylamino pyridine (DMAP) should be used for the reaction at low temperature of about 0° C. On the other hand, the acetolysis of phosphatidyl choline has the yield of about 74.5%, but expensive phosphatidyl choline should be used in a large amount for this method. Therefore, the method is not appropriate to produce the target compound in a large amount.
In order to regioselectively synthesize glycerol derivative having ester groups of different fatty acids at 1 and 2-positions of glycerol and acetyl group at 3-position of glycerol, the following process is carried out in a conventional method. First, an ester group is regioselectively introduced into 1-position of glycerol. Then, hydroxyl group of 3-position of glycerol is protected and other ester group is introduced into 2-position of glycerol. The process can regioselectively introduce ester groups into 1, 2 and 3-positions of glycerol. However, when the protecting group at 3-position is removed for introducing an ester group into 3-position of glycerol, there is a problem that the ester group of 2-position of glycerol is migrated to 3-position of glycerol (J. Org. Chem., 52(22), 4973˜4977, 1987).